(R)-Phenyl­ethanaminium fluoride monohydrate

The title compound, C₈H₁₂FN·H₂O, was crystallized from an aqueous solution. The crystal structure features N—H...F, N—H...O and O—H...F hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.045
• wR factor = 0.113
• Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               1085
           Count of symmetry unique reflns         1103
           Completeness (_total/calc)             98.37%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: maXus (Mackay et al., 1999).

(I)

Crystal data

C8H12N^+·F^−·H2O	F(000) = 344
Mr = 159.20	Dx = 1.135 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 66 reflections
a = 6.1754 (2) Å	θ = 4.6–17.0°
b = 6.6276 (5) Å	µ = 0.09 mm^−1
c = 22.772 (2) Å	T = 299 K
V = 932.01 (11) Å^3	Fragment, colourless
Z = 4	0.60 × 0.23 × 0.15 mm

Data collection

Bruker–Nonius KappaCCD diffractometer	Rint = 0.081
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 4.5°
φ & ω scans	h = −7→5
5560 measured reflections	k = −8→6
1085 independent reflections	l = −27→28
866 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0398P)^2 + 0.166P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
1085 reflections	Δρmax = 0.18 e Å^−3
100 parameters	Δρmin = −0.13 e Å^−3
0 restraints

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4373 (5)	0.1132 (5)	0.11994 (11)	0.0536 (7)
C2	0.2795 (4)	0.2676 (4)	0.14327 (11)	0.0485 (6)
C3	0.0887 (5)	0.3134 (5)	0.11434 (12)	0.0589 (8)
C4	−0.0614 (5)	0.4450 (5)	0.13815 (14)	0.0694 (9)
C5	−0.0226 (7)	0.5308 (6)	0.19190 (15)	0.0768 (10)
C6	0.1657 (7)	0.4889 (6)	0.22120 (14)	0.0831 (11)
C7	0.3180 (6)	0.3578 (5)	0.19700 (12)	0.0677 (9)
C8	0.3602 (7)	−0.1024 (5)	0.13225 (16)	0.0805 (11)
F1	0.6469 (2)	0.4791 (2)	0.01353 (7)	0.0537 (4)
N1	0.4754 (3)	0.1335 (3)	0.05554 (9)	0.0474 (5)
O1	0.7959 (3)	0.8598 (3)	0.03563 (11)	0.0802 (7)
H1A	0.5201	0.2582	0.0476	0.071*
H1B	0.3528	0.1089	0.0363	0.071*
H1C	0.5762	0.0456	0.0443	0.071*
H1O	0.7606	0.7370	0.0274	0.120*
H2O	0.9154	0.8902	0.0181	0.120*
H1	0.5760	0.1328	0.1401	0.064*
H3	0.0607	0.2543	0.0781	0.071*
H7	0.4460	0.3310	0.2171	0.081*
H6	0.1922	0.5483	0.2575	0.100*
H5	−0.1241	0.6175	0.2085	0.092*
H4	−0.1879	0.4752	0.1178	0.083*
H8A	0.4671	−0.1966	0.1186	0.121*
H8B	0.2260	−0.1261	0.1121	0.121*
H8C	0.3391	−0.1197	0.1737	0.121*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0533 (16)	0.0524 (17)	0.0551 (15)	−0.0025 (14)	−0.0024 (13)	0.0155 (13)
C2	0.0544 (15)	0.0450 (15)	0.0462 (13)	−0.0124 (13)	0.0027 (12)	0.0064 (12)
C3	0.0589 (16)	0.0624 (19)	0.0553 (14)	0.0014 (15)	−0.0003 (13)	−0.0107 (14)
C4	0.0671 (19)	0.0629 (19)	0.0782 (19)	0.0036 (18)	0.0088 (17)	−0.0077 (17)
C5	0.096 (2)	0.055 (2)	0.080 (2)	−0.008 (2)	0.030 (2)	−0.0100 (18)
C6	0.126 (3)	0.070 (2)	0.0536 (18)	−0.027 (3)	0.012 (2)	−0.0137 (17)
C7	0.084 (2)	0.068 (2)	0.0512 (16)	−0.019 (2)	−0.0044 (16)	0.0045 (16)
C8	0.096 (3)	0.0528 (19)	0.093 (2)	0.0038 (19)	0.018 (2)	0.0297 (18)
F1	0.0487 (8)	0.0376 (8)	0.0747 (10)	−0.0012 (7)	0.0011 (7)	0.0024 (7)
N1	0.0442 (11)	0.0340 (11)	0.0640 (12)	−0.0017 (11)	0.0033 (10)	0.0043 (10)
O1	0.0557 (11)	0.0407 (11)	0.144 (2)	−0.0031 (11)	0.0237 (13)	−0.0136 (12)

Geometric parameters (Å, º)

N1—C1	1.491 (3)	O1—H1O	0.8632
C1—C2	1.510 (4)	O1—H2O	0.8627
C1—C8	1.532 (5)	C1—H1	0.9800
C3—C2	1.383 (4)	C3—H3	0.9300
C3—C4	1.384 (4)	C7—H7	0.9300
C2—C7	1.383 (4)	C6—H6	0.9300
C7—C6	1.394 (5)	C5—H5	0.9300
C6—C5	1.369 (5)	C4—H4	0.9300
C5—C4	1.371 (5)	C8—H8A	0.9600
N1—H1A	0.8900	C8—H8B	0.9600
N1—H1B	0.8900	C8—H8C	0.9600
N1—H1C	0.8900
N1—C1—C2	112.7 (2)	C2—C1—H1	108.1
N1—C1—C8	108.3 (2)	C8—C1—H1	108.1
C2—C1—C8	111.5 (2)	C2—C3—H3	119.3
C2—C3—C4	121.5 (3)	C4—C3—H3	119.3
C7—C2—C3	118.2 (3)	C2—C7—H7	119.9
C7—C2—C1	119.6 (3)	C6—C7—H7	119.9
C3—C2—C1	122.1 (2)	C5—C6—H6	119.8
C2—C7—C6	120.2 (3)	C7—C6—H6	119.8
C5—C6—C7	120.5 (3)	C6—C5—H5	120.0
C6—C5—C4	120.0 (3)	C4—C5—H5	120.0
C5—C4—C3	119.6 (3)	C5—C4—H4	120.2
C1—N1—H1A	109.5	C3—C4—H4	120.2
C1—N1—H1B	109.5	C1—C8—H8A	109.5
H1A—N1—H1B	109.5	C1—C8—H8B	109.5
C1—N1—H1C	109.5	H8A—C8—H8B	109.5
H1A—N1—H1C	109.5	C1—C8—H8C	109.5
H1B—N1—H1C	109.5	H8A—C8—H8C	109.5
H1O—O1—H2O	109.6	H8B—C8—H8C	109.5
N1—C1—H1	108.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···F1	0.89	1.83	2.699 (2)	164
N1—H1B···F1^i	0.89	1.80	2.673 (3)	166
N1—H1C···O1^ii	0.89	1.84	2.722 (3)	169
O1—H1O···F1	0.86	1.87	2.732 (3)	172
O1—H2O···F1^iii	0.86	1.82	2.663 (2)	165

Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) x, y−1, z; (iii) x+1/2, −y+3/2, −z.